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At least once a month, the cards are stacked against Jitendra Gupta. The managing director of digital payments provider PayU India has to rack his brains to beat some of the best minds in the startup world at his Mumbai residence. However, most of the time, Gupta grins, he has that ace up his sleeve (only metaphorically, of course).

Poker, he reckons, is an intellectually stimulating game that teaches you to read people’s behaviour, their risk-taking appetite and a quick calculation of the odds.

“Poker has helped me evolve as a person in terms of my decision-making abilities,” says Gupta, who has been religiously hosting friendly poker matches among his entrepreneur and investor friends at his home every month. The former entrepreneur, who sold his company Citrus Pay to Nasper-owned PayU for $130 million in an all-cash deal last September, is a regular on the Las Vegas gaming circuit every year and recently bought a team in the Poker Sports League. Other startup artistes — Kunal Shah of FreeCharge, Girish Mathrubootham of Freshdesk and Mithun Sacheti of CaratLane — too bought teams in the professional poker league (see Out of 12 Teams in Poker Sports League...). It’s not only Gupta who gets an intellectual high from the game. Others too are hooked to it and are playing with a full deck.

Take, for instance, Sumeet Khanna, managing partner of online healthcare provider Surgivisor. The entrepreneur contends that poker has taught him certain skills, the biggest being money management and discipline. “My favourite destination for playing the game is Las Vegas,” says Khanna, adding that even the Massachusetts Institute of Technology offers an online course in poker which can be applied to investment management and trading.

Poker Faces Venture capitalist Rutvik Doshi decodes entrepreneurs’ love for the card game which has even Silicon Valley heavyweights like Chamath Palihapitiya — an early Facebook executive who started his venture capital firm Social Capital in 2011 — among its ardent followers. “I am not surprised to see entrepreneurs getting hooked to poker,” says Doshi, a director at the India arm of Inventus Capital Partners, and an avid poker player. A large part of an entrepreneur’s journey gets mirrored in the game. He explains how: Entrepreneurs are risk-taking animal. They place calculated bets against a huge unknown, and they constantly try to anticipate a rival’s moves to adjust their strategy.

“This is exactly what a poker player does on the table,” says Doshi, adding that inherent similarities between poker and startups appeal to an entrepreneur. While Doshi’s first tryst with cards happened in his childhood when his Gujarati family got together during Diwali, Janmashtmi or weddings to play teen patti, it was around 2000 that he got exposed to poker as a professional game in the US. “Poker is one way to relive the thrills of being an entrepreneur,” he adds.

Safe Bet Nobody knows the thrill better than Kunal Shah. The co-founder of digital payments provider FreeCharge, which was bought by Snapdeal in 2015, contends that it’s common among startup founders to play poker for fun. “It’s a great sport that challenges you intellectually,” adds Shah, who early this month joined marque venture capital firm Sequoia Capital as an advisor. “As awareness spreads, a lot of misconceptions around the game will go away,” he adds.

Although poker is wrongly perceived as gambling, entrepreneurs find it a safe bet. Take, for instance, Bengaluru-based entrepreneur Vivek Prakash. Cofounder of online programming platform HackerEarth, Prakash started playing poker in a few clubs in Bengaluru and went to Macau earlier this year to explore the poker scene. “The first few games that I played in clubs boosted my confidence as I could stack up chips easily,” he says. In poker, he lets on, one needs to understand the table, the hand, the kind of players, the odds and dozens of other variables at the same time. While one doesn’t have much time, one must listen to one’s mind to win the racy game. The biggest poker lesson, he says, is that one can always turn the odds in one’s favour.

For Amit Somani, managing partner at early-stage investment fund Prime Ventures, poker is the biggest teacher. The ability to deal with any situation, to read one’s opponents and to have the courage and conviction to play one’s card without the foolhardiness of randomly betting are the three big takeaways, he points out. “It’s a game of probabilities and calculated risk,” says Somani. He may well have been talking about startups.

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